diff --git a/lib/reversetunnel/agent.go b/lib/reversetunnel/agent.go
index 0d2cba35adec1..8cf7a07e3b511 100644
--- a/lib/reversetunnel/agent.go
+++ b/lib/reversetunnel/agent.go
@@ -306,16 +306,25 @@ func (a *Agent) handleGlobalRequests(ctx context.Context, requestCh <-chan *ssh.
 
 			switch r.Type {
 			case versionRequest:
-				err := r.Reply(true, []byte(teleport.Version))
+				// reply with the auth server version
+				pong, err := a.Client.Ping(ctx)
 				if err != nil {
-					log.Debugf("Failed to reply to %v request: %v.", r.Type, err)
+					a.log.WithError(err).Warnf("Failed to ping auth server in response to %v request.", r.Type)
+					if err := r.Reply(false, []byte("Failed to retrieve auth version")); err != nil {
+						a.log.Debugf("Failed to reply to %v request: %v.", r.Type, err)
+						continue
+					}
+				}
+
+				if err := r.Reply(true, []byte(pong.ServerVersion)); err != nil {
+					a.log.Debugf("Failed to reply to %v request: %v.", r.Type, err)
 					continue
 				}
 			default:
 				// This handles keep-alive messages and matches the behaviour of OpenSSH.
 				err := r.Reply(false, nil)
 				if err != nil {
-					log.Debugf("Failed to reply to %v request: %v.", r.Type, err)
+					a.log.Debugf("Failed to reply to %v request: %v.", r.Type, err)
 					continue
 				}
 			}
diff --git a/lib/reversetunnel/srv.go b/lib/reversetunnel/srv.go
index 471e30c88de76..0aba941727cd7 100644
--- a/lib/reversetunnel/srv.go
+++ b/lib/reversetunnel/srv.go
@@ -39,7 +39,6 @@ import (
 	"github.com/gravitational/teleport/lib/sshutils"
 	"github.com/gravitational/teleport/lib/utils"
 
-	"github.com/coreos/go-semver/semver"
 	"github.com/gravitational/trace"
 	"github.com/jonboulle/clockwork"
 	"github.com/prometheus/client_golang/prometheus"
@@ -638,7 +637,7 @@ func (s *server) handleHeartbeat(conn net.Conn, sconn *ssh.ServerConn, nch ssh.N
 	// nodes it's a node dialing back.
 	val, ok := sconn.Permissions.Extensions[extCertRole]
 	if !ok {
-		log.Errorf("Failed to accept connection, missing %q extension", extCertRole)
+		s.log.Errorf("Failed to accept connection, missing %q extension", extCertRole)
 		s.rejectRequest(nch, ssh.ConnectionFailed, "unknown role")
 		return
 	}
@@ -662,7 +661,7 @@ func (s *server) handleHeartbeat(conn net.Conn, sconn *ssh.ServerConn, nch ssh.N
 		s.handleNewCluster(conn, sconn, nch)
 	// Unknown role.
 	default:
-		log.Errorf("Unsupported role attempting to connect: %v", val)
+		s.log.Errorf("Unsupported role attempting to connect: %v", val)
 		s.rejectRequest(nch, ssh.ConnectionFailed, fmt.Sprintf("unsupported role %v", val))
 	}
 }
@@ -670,14 +669,14 @@ func (s *server) handleHeartbeat(conn net.Conn, sconn *ssh.ServerConn, nch ssh.N
 func (s *server) handleNewService(role types.SystemRole, conn net.Conn, sconn *ssh.ServerConn, nch ssh.NewChannel, connType types.TunnelType) {
 	cluster, rconn, err := s.upsertServiceConn(conn, sconn, connType)
 	if err != nil {
-		log.Errorf("Failed to upsert %s: %v.", role, err)
+		s.log.Errorf("Failed to upsert %s: %v.", role, err)
 		sconn.Close()
 		return
 	}
 
 	ch, req, err := nch.Accept()
 	if err != nil {
-		log.Errorf("Failed to accept on channel: %v.", err)
+		s.log.Errorf("Failed to accept on channel: %v.", err)
 		sconn.Close()
 		return
 	}
@@ -689,14 +688,14 @@ func (s *server) handleNewCluster(conn net.Conn, sshConn *ssh.ServerConn, nch ss
 	// add the incoming site (cluster) to the list of active connections:
 	site, remoteConn, err := s.upsertRemoteCluster(conn, sshConn)
 	if err != nil {
-		log.Error(trace.Wrap(err))
+		s.log.Error(trace.Wrap(err))
 		s.rejectRequest(nch, ssh.ConnectionFailed, "failed to accept incoming cluster connection")
 		return
 	}
 	// accept the request and start the heartbeat on it:
 	ch, req, err := nch.Accept()
 	if err != nil {
-		log.Error(trace.Wrap(err))
+		s.log.Error(trace.Wrap(err))
 		sshConn.Close()
 		return
 	}
@@ -1059,27 +1058,12 @@ func newRemoteSite(srv *server, domainName string, sconn ssh.Conn) (*remoteSite,
 	}
 	remoteSite.remoteClient = clt
 
-	// DELETE IN: 8.0.0
-	//
-	// Check if the cluster that is connecting is a pre-v7 cluster. If it is,
-	// don't assume the newer organization of cluster configuration resources
-	// (RFD 28) because older proxy servers will reject that causing the cache
-	// to go into a re-sync loop.
-	var accessPointFunc auth.NewCachingAccessPoint
-	ok, err := isPreV7Cluster(closeContext, sconn)
+	remoteVersion, err := getRemoteAuthVersion(closeContext, sconn)
 	if err != nil {
 		return nil, trace.Wrap(err)
 	}
-	if ok {
-		log.Debugf("Pre-v7 cluster connecting, loading old cache policy.")
-		accessPointFunc = srv.Config.NewCachingAccessPointOldProxy
-	} else {
-		accessPointFunc = srv.newAccessPoint
-	}
 
-	// Configure access to the cached subset of the Auth Server API of the remote
-	// cluster this remote site provides access to.
-	accessPoint, err := accessPointFunc(clt, []string{"reverse", domainName})
+	accessPoint, err := createRemoteAccessPoint(srv, clt, remoteVersion, domainName)
 	if err != nil {
 		return nil, trace.Wrap(err)
 	}
@@ -1124,33 +1108,35 @@ func newRemoteSite(srv *server, domainName string, sconn ssh.Conn) (*remoteSite,
 	return remoteSite, nil
 }
 
-// DELETE IN: 8.0.0.
-//
-// isPreV7Cluster checks if the cluster is older than 7.0.0.
-func isPreV7Cluster(ctx context.Context, conn ssh.Conn) (bool, error) {
-	version, err := sendVersionRequest(ctx, conn)
+// createRemoteAccessPoint creates a new access point for the remote cluster.
+// Checks if the cluster that is connecting is a pre-v7 cluster. If it is,
+// don't assume the newer organization of cluster configuration resources
+// (RFD 28) because older proxy servers will reject that causing the cache
+// to go into a re-sync loop.
+func createRemoteAccessPoint(srv *server, clt auth.ClientI, version, domainName string) (auth.AccessPoint, error) {
+	ok, err := utils.MinVerWithoutPreRelease(version, utils.VersionBeforeAlpha("7.0.0"))
 	if err != nil {
-		return false, trace.Wrap(err)
+		return nil, trace.Wrap(err)
 	}
 
-	remoteClusterVersion, err := semver.NewVersion(version)
-	if err != nil {
-		return false, trace.Wrap(err)
+	accessPointFunc := srv.Config.NewCachingAccessPoint
+	if !ok {
+		srv.log.Debugf("cluster %q running %q is connecting, loading old cache policy.", domainName, version)
+		accessPointFunc = srv.Config.NewCachingAccessPointOldProxy
 	}
-	minClusterVersion, err := semver.NewVersion(utils.VersionBeforeAlpha("7.0.0"))
+
+	// Configure access to the cached subset of the Auth Server API of the remote
+	// cluster this remote site provides access to.
+	accessPoint, err := accessPointFunc(clt, []string{"reverse", domainName})
 	if err != nil {
-		return false, trace.Wrap(err)
-	}
-	// Return true if the version is older than 7.0.0
-	if remoteClusterVersion.LessThan(*minClusterVersion) {
-		return true, nil
+		return nil, trace.Wrap(err)
 	}
 
-	return false, nil
+	return accessPoint, nil
 }
 
-// sendVersionRequest sends a request for the version remote Teleport cluster.
-func sendVersionRequest(ctx context.Context, sconn ssh.Conn) (string, error) {
+// getRemoteAuthVersion sends a version request to the remote agent.
+func getRemoteAuthVersion(ctx context.Context, sconn ssh.Conn) (string, error) {
 	errorCh := make(chan error, 1)
 	versionCh := make(chan string, 1)
 
@@ -1164,6 +1150,7 @@ func sendVersionRequest(ctx context.Context, sconn ssh.Conn) (string, error) {
 			errorCh <- trace.BadParameter("no response to %v request", versionRequest)
 			return
 		}
+
 		versionCh <- string(payload)
 	}()
 
@@ -1175,7 +1162,7 @@ func sendVersionRequest(ctx context.Context, sconn ssh.Conn) (string, error) {
 	case <-time.After(defaults.WaitCopyTimeout):
 		return "", trace.BadParameter("timeout waiting for version")
 	case <-ctx.Done():
-		return "", ctx.Err()
+		return "", trace.Wrap(ctx.Err())
 	}
 }
 
diff --git a/lib/reversetunnel/srv_test.go b/lib/reversetunnel/srv_test.go
index 01a04d91fe303..e6747d7f59a08 100644
--- a/lib/reversetunnel/srv_test.go
+++ b/lib/reversetunnel/srv_test.go
@@ -18,6 +18,7 @@ package reversetunnel
 
 import (
 	"context"
+	"errors"
 	"net"
 	"testing"
 	"time"
@@ -160,3 +161,70 @@ type mockAccessPoint struct {
 func (ap mockAccessPoint) GetCertAuthority(ctx context.Context, id types.CertAuthID, loadKeys bool, opts ...services.MarshalOption) (types.CertAuthority, error) {
 	return ap.ca, nil
 }
+
+func TestCreateRemoteAccessPoint(t *testing.T) {
+	cases := []struct {
+		name           string
+		version        string
+		assertion      require.ErrorAssertionFunc
+		oldRemoteProxy bool
+	}{
+		{
+			name:      "invalid version",
+			assertion: require.Error,
+		},
+		{
+			name:      "remote running 8.0.0",
+			assertion: require.NoError,
+			version:   "8.0.0",
+		},
+		{
+			name:      "remote running 7.0.0",
+			assertion: require.NoError,
+			version:   "7.0.0",
+		},
+		{
+			name:           "remote running 6.0.0",
+			assertion:      require.NoError,
+			version:        "6.0.0",
+			oldRemoteProxy: true,
+		},
+		{
+			name:           "remote running 5.0.0",
+			assertion:      require.NoError,
+			version:        "5.0.0",
+			oldRemoteProxy: true,
+		},
+	}
+
+	for _, tt := range cases {
+		t.Run(tt.name, func(t *testing.T) {
+			newProxyFn := func(clt auth.ClientI, cacheName []string) (auth.AccessPoint, error) {
+				if tt.oldRemoteProxy {
+					return nil, errors.New("expected to create an old remote proxy")
+				}
+
+				return nil, nil
+			}
+
+			oldProxyFn := func(clt auth.ClientI, cacheName []string) (auth.AccessPoint, error) {
+				if !tt.oldRemoteProxy {
+					return nil, errors.New("expected to create an new remote proxy")
+				}
+
+				return nil, nil
+			}
+
+			clt := &mockAuthClient{}
+			srv := &server{
+				log: utils.NewLoggerForTests(),
+				Config: Config{
+					NewCachingAccessPoint:         newProxyFn,
+					NewCachingAccessPointOldProxy: oldProxyFn,
+				},
+			}
+			_, err := createRemoteAccessPoint(srv, clt, tt.version, "test")
+			tt.assertion(t, err)
+		})
+	}
+}
diff --git a/lib/utils/ver.go b/lib/utils/ver.go
index e362c6496deeb..71e967d7fffed 100644
--- a/lib/utils/ver.go
+++ b/lib/utils/ver.go
@@ -45,3 +45,32 @@ func CheckVersion(currentVersion, minVersion string) error {
 func VersionBeforeAlpha(version string) string {
 	return version + "-aa"
 }
+
+// MinVerWithoutPreRelease compares semver strings, but skips prerelease. This allows to compare
+// two versions and ignore dev,alpha,beta, etc. strings.
+func MinVerWithoutPreRelease(currentVersion, minVersion string) (bool, error) {
+	currentSemver, minSemver, err := versionStringToSemver(currentVersion, minVersion)
+	if err != nil {
+		return false, trace.Wrap(err)
+	}
+
+	// Erase pre-release string, so only version is compared.
+	currentSemver.PreRelease = ""
+	minSemver.PreRelease = ""
+
+	return !currentSemver.LessThan(*minSemver), nil
+}
+
+func versionStringToSemver(ver1, ver2 string) (*semver.Version, *semver.Version, error) {
+	v1Semver, err := semver.NewVersion(ver1)
+	if err != nil {
+		return nil, nil, trace.Wrap(err, "unsupported version format, need semver format: %q, e.g 1.0.0", v1Semver)
+	}
+
+	v2Semver, err := semver.NewVersion(ver2)
+	if err != nil {
+		return nil, nil, trace.Wrap(err, "unsupported version format, need semver format: %q, e.g 1.0.0", v2Semver)
+	}
+
+	return v1Semver, v2Semver, nil
+}